Chapter Text
After Dean dropped Sam off, Sam went inside his shared apartment with Jess. He saw her sleeping in their bedroom. He showered and changed his clothes. In the morning he woke up without Jess by his side, he went to check on the kitchen and saw her. They ate breakfast and went to College. Afterwards, he wanted to talk about his ‘hunting trip’ with his family to Jess. She was shocked to learn about the supernatural. When he finished explained about it, Jess was worried about Sam about him hunting down demons. He said that he’ll go hunting with his brother to look for his father but once in awhile. After some time Dean and Sam met Bobby on a hunting trip. They talked and they created a bond with Bobby. They saw Bobby as a father figure or more like a father than their real father. They stopped talking to John and they went to therapy for their childhood trauma. John got arrested for charges of child neglect, abuse and mistreatment them. A few months later they met someone named Charlie Bradbury and Dean and Sam became her friends. A year later Charlie went missing mysteriously, Bobby, Sam and Dean started looking for her. Jess was searching in her apartment and her job, and asking Charlie friends if they have seen her while the others went looking where her family lived. Her family lived 7 hours away from them. They couldn’t find her anywhere, they looked, searched for weeks but couldn’t find nothing. After some time they slowly stopped looking for her. Time to time they looked for something just to see her again. Dean and Sam thought about Charlie as a little sister they never had, while Bobby thought about her as a daughter. After 2 years Sam and Jess decided to get married. Sam says “Will you marry me?”, then Jess said “ Yes. ” They prepare for the wedding, went shopping for their wedding outfits, they went looking for the venue, the photographer, the videographer, choose the food and drinks, for Jess makeup and hair, for the transportation, the clean up crew, their vows, finding their florist, their wedding invitation and etc. After a year they had everything ready to get married. Both of them woke up early and got ready for their wedding. Bobby and Dean went to Sam to help him, Jess has her friends helping her getting ready. After hours of getting ready and waiting the guests arrived at the Venue. Sam got first to the altar, then Bobby walked down the aisle with Jess. Sam though about how beautiful Jess looked in the Dress. After they say ‘ I do’ and their vows to each other they began to move outside. The next morning Sam took Jess to their honeymoon. Dean is excited that he has a sister - in - law. Sam combined their last names so it’s Sam Moore Winchester and Jessica Moore Winchester. Years has pass between them, Jess is 4 months pregnant with their first child. Sam invited his brother and Bobby to their gender reveal party. Dean and Bobby came and they started having fun. After they revealed that their having a girl, Dean and Bobby helped them clean up the mess and headed to their houses. Dean was happy for them. Sam graduated with his degree and started working on being a lawyer. Jess graduated with a degree and started working as a nurse. They got a house with 2 floors, 4 bedrooms and 3 bathrooms with a small pool. Dean and Bobby sometimes stay overnight or when they are closer to the hunting area. He stopped going on hunting trips since he’s having a baby in 5 months. He promised to Jess that he wouldn’t be hunting again ever only if his brother needed help or in danger. Sam found out that Dean is dating someone. Dean brought Castiel to dinner to meet his brother and sister in law. He told Sam that Castiel is an angel and has a kid named Jack that has 4 years old. Sam is happy that his brother started dating and raising a kid with his boyfriend. Dean said “ We’re getting married after 3 months after the kid is born.” Sam says “Wait really? Congratulations on getting married” Dean says “ Thanks.” Later that week, Dean brought Jack to meet his uncle and aunt. Sam thought that the kid was cute and a ball of sunshine. After the baby is born, Dean and Castiel started on planning their wedding that’s happening in 8 - 10 months. Jack was happy that he has another dad and that he has more family members. He thinks that Jess is a sweet, kind and a great aunt. Dean, Cass and Jack went to visit Sam and Jess for their baby. When they arrived, they got them gifts for the baby. Dean took care of the baby while Jess took a nap. Dean asked Sam “What’s her name.” Sam says “ Charlie in honor of her ”. Dean says “ It’s a great name. It’s good to remember her.” After they left their house, Dean carried Jack to the car because he fell asleep. They started looking for their Venue, their invites, their rings, vows, marriage certificates, tables, chairs, photographer, their transportation, and etc. Both of them talked about how Jack should be the Florist for their wedding day.